(E)-2-(2-(3-Ethoxy-3-oxoprop-1-enyl)-6-fluorophenyl)acetic acid

(E)-2-(2-(3-Ethoxy-3-oxopropyl-1-enyl)-6-fluorophenyl)acetic acid



.

RM,
 2-fluorophenylacetic acid (1a)
 N-acetyl isoleucine, (3077-46-1)
 ethyl acrylate (2a)(451-82-1)

TLC (hexanes:EtOAc:HOAc, 66:33:1) R_f = 0.29;






M.p = 97-99 °C;



¹H NMR (600 MHz, CDCl₃) δ: 1.33 (t, J = 7.2 Hz, 3 H), 3.87 (d, J = 1.8 Hz, 2 H), 4.27 (q, J = 6.6 Hz, 2 H), 6.38 (d, J = 15.6 Hz, 1 H), 7.10 (t, J = 9.6 Hz, 1 H), 7.29 (td, J₁ = 8.4, J₂ = 6.0 Hz, 1 H), 7.38 (d, J = 7.8 Hz, 1 H), 7.84 (d,J = 15.6 Hz, 1 H);  

predict

¹³C NMR (150 MHz, CDCl₃) δ: 14.2, 30.5 (d, J_C-F = 5.1 Hz), 60.9, 116.5 (d, J _C-F = 22.7 Hz), 120.5 (d, J_C-F = 16.1 Hz), 122.1, 122.5 (d, J_C-F = 3.2 Hz), 129.1 (d, J_C-F = 9.0 Hz), 136.3 (d, J_C-F = 3.5 Hz), 140.3 (d, J_C-F = 3.4 Hz), 161.4 (d, J_C-F = 245.6 Hz), 166.5, 175.9;

Decoupled ¹⁹F NMR (375 MHz, CDCl₃) δ: -115.11 (s, 1 F);

 IR (film): 2984, 1735, 1705, 1638, 1574, 1462, 1369, 1318, 1264, 1241, 1183, 1156, 1001, 971, 866, 802 cm^-1;


HRMS (ESI-TOF) m/z calcd for C₁₃H₁₄FO₄ [M+H]⁺: 253.0876, found: 253.0871;


Anal. calcd. for C₁₃H₁₃FO₄: C 61.90, H 5.20, F 7.53, found: C 62.07, H 5.36, F 7.42.





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